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- Cyclododecahexaene abstract "Cyclododecahexaene or [12]annulene (C12H12) is a member of a series of annulenes with some interest in organic chemistry with regard to the study of aromaticity These compounds are in general unstable due to their antiaromaticity and built-up of steric strain. On the other hand the di-anion with 14 electrons is a Hückel aromat and more stable. According to in silico experiments the tri-trans isomer is expected to be the most stable, followed by the 1,7-ditrans and the all cis-isomers (+1 kcal/mol) and by the 1,5-ditrans isomer (+5 kcal/mol). The first [12]annulene with sym-tri-trans configuration was synthesized in 1970 from a tricyclic precursor by photolysis at low temperatures. On heating the compound rearranges to a bicyclic [6,4,0] isomer. Reducing the compound at low temperatures allowed analysis of the dianion by proton NMR with the inner protons resonating at - 4.5 ppm relative to TMS, evidence of an aromatic diamagnetic ring current.In one study the 1,7-ditrans isomer is generated at low temperatures in THF by dehydrohalogenation of a hexabromocyclododecane with potassium tert-butoxide. Reduction of this compound at low temperature with caesium metal leads first to the radical anion and then to the dianion. The chemical shift for the internal protons in this compound is with +0.2 ppm much more modest than in the tri-trans isomer.Heating the radical ion solution to room temperature leads to loss of one equivalent of hydrogen and formation of the heptalene radical anion.".
- Cyclododecahexaene thumbnail 12-annulene.svg?width=300.
- Cyclododecahexaene wikiPageID "8019803".
- Cyclododecahexaene wikiPageLength "2199".
- Cyclododecahexaene wikiPageOutDegree "27".
- Cyclododecahexaene wikiPageRevisionID "648242178".
- Cyclododecahexaene wikiPageWikiLink Anion.
- Cyclododecahexaene wikiPageWikiLink Annulene.
- Cyclododecahexaene wikiPageWikiLink Antiaromaticity.
- Cyclododecahexaene wikiPageWikiLink Aromatic.
- Cyclododecahexaene wikiPageWikiLink Aromatic_ring_current.
- Cyclododecahexaene wikiPageWikiLink Aromaticity.
- Cyclododecahexaene wikiPageWikiLink Bicyclic.
- Cyclododecahexaene wikiPageWikiLink Bicyclic_molecule.
- Cyclododecahexaene wikiPageWikiLink Caesium.
- Cyclododecahexaene wikiPageWikiLink Category:Annulenes.
- Cyclododecahexaene wikiPageWikiLink Category:Antiaromatic_compounds.
- Cyclododecahexaene wikiPageWikiLink Chemical_shift.
- Cyclododecahexaene wikiPageWikiLink Cis–trans_isomerism.
- Cyclododecahexaene wikiPageWikiLink Dehydrohalogenation.
- Cyclododecahexaene wikiPageWikiLink Diamagnetic_ring_current.
- Cyclododecahexaene wikiPageWikiLink Heptalene.
- Cyclododecahexaene wikiPageWikiLink Hxc3xbcckels_rule.
- Cyclododecahexaene wikiPageWikiLink In_silico.
- Cyclododecahexaene wikiPageWikiLink Ion.
- Cyclododecahexaene wikiPageWikiLink Organic_chemistry.
- Cyclododecahexaene wikiPageWikiLink Organic_redox_reaction.
- Cyclododecahexaene wikiPageWikiLink Organic_reduction.
- Cyclododecahexaene wikiPageWikiLink Photodissociation.
- Cyclododecahexaene wikiPageWikiLink Photolysis.
- Cyclododecahexaene wikiPageWikiLink Potassium_tert-butoxide.
- Cyclododecahexaene wikiPageWikiLink Proton_NMR.
- Cyclododecahexaene wikiPageWikiLink Proton_nuclear_magnetic_resonance.
- Cyclododecahexaene wikiPageWikiLink Radical_anion.
- Cyclododecahexaene wikiPageWikiLink Radical_ion.
- Cyclododecahexaene wikiPageWikiLink Room_temperature.
- Cyclododecahexaene wikiPageWikiLink Steric_strain.
- Cyclododecahexaene wikiPageWikiLink Tetrahydrofuran.
- Cyclododecahexaene wikiPageWikiLink Trans_isomer.
- Cyclododecahexaene wikiPageWikiLink Van_der_Waals_strain.
- Cyclododecahexaene wikiPageWikiLink File:12-annulene.svg.
- Cyclododecahexaene wikiPageWikiLink File:12annulene2006.png.
- Cyclododecahexaene wikiPageWikiLinkText "[12]annulene".
- Cyclododecahexaene wikiPageWikiLinkText "cyclododecahexaene".
- Cyclododecahexaene hasPhotoCollection Cyclododecahexaene.
- Cyclododecahexaene wikiPageUsesTemplate Template:Annulenes.
- Cyclododecahexaene wikiPageUsesTemplate Template:Refimprove.
- Cyclododecahexaene wikiPageUsesTemplate Template:Reflist.
- Cyclododecahexaene subject Category:Annulenes.
- Cyclododecahexaene subject Category:Antiaromatic_compounds.
- Cyclododecahexaene hypernym Member.
- Cyclododecahexaene type Article.
- Cyclododecahexaene type Person.
- Cyclododecahexaene type Article.
- Cyclododecahexaene type Cycloalkene.
- Cyclododecahexaene type Hydrocarbon.
- Cyclododecahexaene comment "Cyclododecahexaene or [12]annulene (C12H12) is a member of a series of annulenes with some interest in organic chemistry with regard to the study of aromaticity These compounds are in general unstable due to their antiaromaticity and built-up of steric strain. On the other hand the di-anion with 14 electrons is a Hückel aromat and more stable.".
- Cyclododecahexaene label "Cyclododecahexaene".
- Cyclododecahexaene sameAs m.026nscb.
- Cyclododecahexaene sameAs Q5198699.
- Cyclododecahexaene sameAs Q5198699.
- Cyclododecahexaene wasDerivedFrom Cyclododecahexaene?oldid=648242178.
- Cyclododecahexaene depiction 12-annulene.svg.
- Cyclododecahexaene isPrimaryTopicOf Cyclododecahexaene.